Potassium Cyanide → 2-(4-Benzyloxyphenyl)-2-(N,N-diethylamino)acetonitrile

HRID 1379686Notes

Reaction equation

HRID 1379686 reaction equation
Cl.[CH2:2]([NH:4][CH2:5][CH3:6])[CH3:3].[C-:7]#[N:8].[K+].CO.C1COCC1.[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[CH2:17]([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]([N:4]([CH2:5][CH3:6])[CH2:2][CH3:3])[C:7]#[N:8])=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 10197650Diethylammonium chlorideHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 189237822-(4-Benzyloxyphenyl)-2-(N,N-diethylamino)acetonitrileYield 589%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diethylamine hydrochloride (76.7 g, 70 mmol) was added portion wise at rt to a 200 mL aqueous solution of potassium cyanide (45.5 g, 70 mmol) with stirring and warmed to 60°-65° C. A MeOH/THF (300 ml, 1:1) solution of 4-(benzyloxy)-benzaldehyde (100 g, 47 mmol) (Aldrich) was added in a thin stream to the aqueous solution and stirred for 16 hr at ~62° C. The reaction mixture was allowed to cool and the organics were removed in vacuo. The aqueous portion was diluted with an equal volume of brine and extracted several times with EtOAc. The EtOAc extracts were combined, washed with H2O, dried (Na2SO4), and concentrated to a tacky amber solid. The material was triturated with petroleum ether and filtered to give a yellow solid, which was taken up in warm Et2O, charcoaled, filtered, diluted with petroleum ether, and allowed to crystallize. The crystals were filtered and dried in vacuo to give 81.5 g (59%) of the desired product: mp 75°-76° C.; 1H NMR (CDCl3) d 1.06-1.11 (t, 6H, J=7 Hz, CH3), 2.42-2.49 (m, 2H, NCH2), 2.66-2.73 (m, 2H, NCH2), 4.98 (s, 1H, CHCN), 5.09 (s, 2H, OCH2), 6.99-7.01 (d, 2H, J=7 Hz, ArH), 7.35-7.49 (m, 7H, ArH); MS(FD) 294(M+). Anal. Calcd for C19H22N2O: C, 77.52; H, 7.53; N, 9.51. Found: C, 77.70; H, 7.64; N, 9.45.

Workup

  1. temperaturewarmed to 60°-65° C
  2. stirringstirred for 16 hr at ~62° C
  3. temperatureto cool
  4. customthe organics were removed in vacuo
  5. additionThe aqueous portion was diluted with an equal volume of brine
  6. extractionextracted several times with EtOAc
  7. washwashed with H2O
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to a tacky amber solid
  10. customThe material was triturated with petroleum ether
  11. filtrationfiltered
  12. customto give a yellow solid, which
  13. filtrationfiltered
  14. additiondiluted with petroleum ether
  15. customto crystallize
  16. filtrationThe crystals were filtered
  17. customdried in vacuo

Sources & evidence

ORD record
ord-48cf08abd3ae49709cbdf38b9e116baa
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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